Pivaloyl chloride → Ethyl N-benzyl-N-((tert-butoxycarbonyl)-L-valyl)glycinate

HRID 1456646Notes

Reaction equation

HRID 1456646 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.CC(C)(C)C(Cl)=O.[CH2:32]([O:34][C:35](=[O:45])[CH2:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:33]>C(Cl)Cl>[CH2:32]([O:34][C:35](=[O:45])[CH2:36][N:37]([C:13](=[O:15])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH:10]([CH3:11])[CH3:12])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:33]

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 80908N-Benzylglycine ethyl esterHCID 81531DiisopropylethylamineHCID 83693Boc-L-Valine

Product 1

HCID 23402347Ethyl N-benzyl-N-((tert-butoxycarbonyl)-L-valyl)glycinateYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Boc-valine (2.18 g, 10 mmol) and DIEA (4.4 mL, 25.3 mmol) in CH2Cl2 (20 mL) at -20° C. was added trimethylacetyl chloride (1.2 mL, 9.7 mmol). After stirring for 30 min, compound 701 (2.18 g, 10 mmol) was added and the reaction allowed to warm to rt and stir for 5 hr. The reaction was concentrated in vacuo and the residue taken up into EtOAc and H2O. The layers were separated and the organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine, dried over MgSO4, filtered and concentrated in vacuo to provide 3.45 g of compound 702. ##STR81##

Workup

  1. stirringstir for 5 hr
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe layers were separated
  4. washthe organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59491923daae41ca8b468306e888c426
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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